


The Mighty Frights

by Kit_Cat03



Category: Critical Role (Web Series)
Genre: Alternate Universe - College/University, Alternate Universe - Modern Setting, F/F, F/M, Halloween, Halloween Costumes, Spooky
Language: English
Status: In-Progress
Published: 2020-10-07
Updated: 2020-10-16
Packaged: 2021-03-07 21:20:37
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 2
Words: 2,969
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26884285
Author URL: https://archiveofourown.org/users/Kit_Cat03/pseuds/Kit_Cat03
Summary: A fun cute Halloween AU with our favorite group the mighty nine. Caleb agrees to go volunteer with Beau at the annual charity haunted house her friend runs. This year it seems Jester was able to convenience the owner of the charity to give even more freedom to run with her crazy ideas. A new location, spooky urban legends, a bit of mystery what better place for a new romance to blossom. It won't be that simple though cause while decorating might be Jester's forte talking to boys never really has been. Add in Caleb's awkwardness and lack of social skills and they're bound to need a little bit of help.
Relationships: Beauregard Lionett/Yasha, Jester Lavorre/Caleb Widogast
Comments: 3
Kudos: 45





	1. Chapter 1

**Author's Note:**

> Been in the mood to write a cute spooky fic for the season. This more of a cute little intro, I hope to have the first real chapter up by later today if I don't have anything come up, oh the joys of adulting. Also not too keen on the name still so if you guys have any suggestions.

The cold fall air twisted the leaves outside the coffee shop. Today was the committee meeting where everyone was going to decide the theme and be given their roles. Caleb was a newly indited member of the committee by the request of Beauregard after finding out their friend Molly wasn’t going to be able to participate this year. Caleb sat awkwardly sipping his coffee as the group surrounding him chatted away. He should of know this was going to happen when his roommate, Beau, begged him to come work the haunted house with her. It’s not like these people were strangers to him he met them plenty of times before around the college but never really spent much time with them outside of small talk and class. He wasn’t fond of group activities though normally that would be fine. He would just chat with Beau and let her lead him into new conversations, but she was currently preoccupied trying to flirt with Yasha. To avoid looking awkward Caleb goes back to staring out into the busy downtown streets, where he just catches the glimpse of a girl with blue hair tripping over the curb, scattering all her notebooks and papers on the floor. He immediately gets up and heads outside, the rest of the group too occupied in their conversations to notice. She’s hunched over trying to collect all of her papers before they fly away in the wind.

“Are you alright?” Caleb starts gathering as many papers as he can, clasping them under his arm.

“Yea, I am okay just a bit clumsy at times, thank you for helping me. If it wasn’t for you I’d be running halfway the block trying to gather them all.”

Caleb goes to pick up her thick binder still laying on the floor and hands it to her, papers still tightly under his shoulder.

“It’s nothing really, I was just having a coffee with friends while we wait for our meeting.”

A smile appears her face, “Oh you must be Cayleb, Beau’s roommate.” She paused for a second looking him over confused, “You don’t look like a dirty hobo.”

Caleb turns to her confused, “Thank you?”

Panic immediately sets in as Jester realized what she just said, “No you see what I meant was its cause like Beau had described you as like this dirty hobo looking type so I was expecting more of a gross mess but like you clearly are far from that like you look really hot and cool and I-” She awkwardly offers him her hand, “Hi I’m Jester.”

Still trying to catch half of what she said, he takes her hand and gives it a small awkward shake, “Caleb Widogast.”

Jester gives him a big smile to hide her utter embarrassment, _That’s what I though._

They stand there in silence for a moment before Caleb speaks up again, pointing towards her car where a cute little purse with glittery black cats laid.

“Well everyone is waiting for you inside here let me take these for you so you can go get your bag.”

She obliges handing over the binder and paper, watching him make his way back to the front entrance. As she turns to go get her purse, she sees all her friends watching from the window intently. _Smooth Jester Smooth_


	2. Intimate Relationship with the floor?

**Notes for the Chapter:**

> Fair warning I wrote after finishing a six-page paper and a neuroscience exam so if there are some grammar mistakes pls go essay on me my brain is fried. Also, I am sorry I lowkey made Fjord seem kind of suck in this chapter. I didn't mean to it just kind of happened. Love him don't mean anything bad by him just need some internal confect for a later part in the story. Hope you guys enjoy

Caleb awkwardly stumbles back into the building books and paper in hand. The group has seemed to have returned to their individual conversations as he places Jester’s things on the table. Though he could feel the familiar gaze of Beauregard eyeing him as she chatted with Yasha. He’s almost made it all the way back to his seat when Beau grabs his shoulder.

“Why don’t you go get Jessie a hot chocolate?” 

Caleb sighs, “Beauregard-”

“Come on Caleb she could really use it, poor girl literally just took a tumble.”

“Why don’t you get it for her then?”

Beau gives him a look that can only be described as light frustration mixed with a bit of, he can’t be serious right now.

“Hey dude I’ll gladly give you the cash, I just think she’ll appreciate it more if you hand it to her. Plus, hot cocoa and sugar cookies are her favorite.” Beau hands Caleb a ten-dollar bill and pushes him towards the register.

He lets out another sigh, reluctantly making his way to the counter. It’s not that he didn’t want to do something nice for Jester, he just didn’t want to embarrass himself. _Pretty girls like her don’t pay attention to dorky nerds like me. What type of game is Beauregard playing?_ Just as the barista hands Caleb the drink, Jester strolls into the shop a little less pep in her step than usual. Awkwardly looking down at her combat boots as she makes her way to the table to begin fixing the mess that is now her binder and papers. The group seems to be in an unspoken agreement to allow Jester to reconfigure herself, none of them pushing her to begin the meeting. Caleb makes his way back to the group hot cocoa in hand, awkwardly placing it in front of Jester. She looks up from her papers with a small smile on her lips as she takes a sip, her curled blue hair obscuring her blushing cheeks.

“Thank you Cayleb.”

Caleb only offers her a nod before making his way to his seat, ready for her presentation. Jester can see him fidgeting with his car keys as she gathers her schedules and lists. She keeps finding herself distracted by the movement, having to remind herself of the task at hand. Jester takes another sip of her drink before mentally trying to hype herself up. She didn’t understand why she was so nervous she had been running this haunted house since she was a freshman in high school. _Come on Jester pull yourself together, you’re just talking to your friends. So, you embarrassed yourself in front of Beau’s super cute roommate, he seems to be a good sport about it._ She takes one more sip before beginning her cheerful speech.

“Okay, you guys time to start our meeting.”

Everyone dissolves their conversations and gives Jester their undivided attention. She seems to get a bit more confidence back as she sees all of her friends intrigued face.

“So, first off I got some really exciting news, I talked to Arty and he was able to get us a permanent location for the haunted house and well any other charity events we want to hold.”

The entire group looks at her surprised, they had been looking for a permanent location for over two years now. Real estate was a rare thing in their small town, especially when it came to large spaces. Everyone’s excitement makes Jester completely forget about feeling self-conscious earlier and she begins excitedly explaining the details to the group.

“Best of all, it’s Whitestone Manor!”, Jester cheered excitedly.

With the mention of Whitestone manor, everyone froze in shock trying to figure out if they heard her right.

Cad turns to Jester, “Whitestone manor? As in the really big mansion in the center of the historic district?”

Caleb adds to his confusion, “The building that at one point in history was literally our town’s city hall?”

“The place that is practically a castle and literally has a small park as its front yard?” Fjord adds.

Jester nods excitedly, “Yup! That’s the one.”

Beau looks at Jester a little weary, “I knew that Artagan was rich and all, but I didn’t realize he was rich enough to buy what is practically a piece of our city's history.”

“Well yea apparently the cities been trying to get someone to take it off their hands for a while the building itself hasn’t been used in over a few decades now. So, when Arty heard about it he offered the city some money to take it off their hands.”

Caleb was in shock; he had heard rumors about the mysterious old man known as Artagan. He was something of a Gatsby in his youth, entertaining the wealthy with his exorbitant parties. The source of his money was always shrouded in mystery, many believing his work had roots in more illegal activities. In his older years though he has calm down quite a bit; giving money to the poor, sponsoring a scholarship program at their local university, even started a small unnamed charity that would do holiday events to raise money and bring awareness for those in need. Many people passed his generosity off as him looking for an easy tax return, but it still didn’t diminish from the positive impact he had on the community.

“I haven’t even told you guys the best part. I got the okay from Arty to expand our spooky endeavors, this year we're not only going to have a haunted house but a whole festival!”

Fjord looks at her concerned, “Jessie are you sure we can handle that?”

She turns to Fjord slightly annoyed at his negatively, “Ugh don’t be such a buzz kill Fjord, of course we can. Just cause you think I am irresponsible and can’t handle things doesn’t make it true.”

Jester stares at Fjord with her arms crossed. Things had been a bit rough between them since their breakup. It’s not like they even ended on bad terms per say either; they had both agreed the relationship just wasn’t working out. It wasn’t till it was revealed that Fjord had been spilling his guts to Avantika, that problems emerge. Talking to Avantika while already an uncomfortable thing for Jester to find out only got significantly worst when he let it slip why. ‘ _Jester please don’t be upset with me it’s not what you think. I just needed to talk with someone who could handle and understand everything I was going through; you know someone a bit more mature._ To Jester, it was like a punch in the gut. She knew she came off as youthful, but she never realized Fjord saw her as a child. Jester was mortified and deeply embarrassed. She questioned her entire relationship with Fjord and beyond. She felt hurt, lied to, and betrayed by who she thought was her first love. When it came to this year’s haunted house the group had told her they’d understand if she wanted him to sit out this year. Jester insisted though that it was fine, stating she was over the whole thing. Beau questioned if they should take things it into their own hands, but the group had talked her out of it.

Right about now Beau was starting to regret not taking things into her own hands as she feels the growing tension between the two _. Ugh, this is exactly what I was afraid of._ Beau looks around at her friends staring in disbelief. _And I’m going to have defuse this of course!_

“I’m sure it’s going to turn out great Jessie. Why don’t you start giving us our roles so we can get started on prep?”

Jester shrugged off her discomfort and compose back to her cheery self.

“Yes of course.” Jester begins handing out everyone’s individual assignments.

She tries to catch sight of Caleb from her peripheral, hoping she didn’t come off bad for a second time today. To her semi relief, he seems more concerned than appalled by the entire situation. Unbeknownst to her Caleb had whispered to Beau.

“What was that about?”

“Fjord is Jester’s ex, let’s just say their relationship ending a bit rocky.”

Caleb nodded slowly looking over to the very tall, broad-shouldered Fjord, he was incredibly handsome. It was altogether an uncomfortably familiar sight; his high school girlfriend Astrid had left him for someone terribly similar to Fjord stature. _Ja, you can’t compete with that. Her going out with you after him would be the biggest disappointment of her life._ His shoulders deflated a bit just thinking about how ridiculous he must have looked buying Jester that coffee earlier. Beau notices and smacks him in the chest.

“Stop it.”

Caleb straitens up a bit though he still is significantly more slouched than before. He watches as Jester talks to Fjord and Cad about their part in the festival. She seems to be mainly putting her attention to Cad though is still Fjord nodding along while they converse. She then makes her way to Veth and Yeza, Caleb knew the couple well for they lived in the apartment across the hall. Veth would always make enough dinner to send some over every evening, even inviting them to have breakfast at their place on Sundays. Jester then made her way to Yasha and Beau, in which Caleb did his best to seem distracted by his phone. The other pairs had left at this point in order to get a head start on preparations. Caleb suddenly feels Beau grab his keys from the table.

“You don’t mind if me and Yasha barrow your car right. Great!”

Before he can even answer, they're off towards his car. _Beauregard, you better not reck my car again_. Jester has taken this chaotic moment as a chance to move closer to Caleb now sitting in what was once Beau’s seat. She watches as he let out a heavy sigh as he watches Yasha and Beau run off with his car keys. She couldn’t help but giggle, it was a well-known thing between the group to never let Beau drive. The girl was the queen of getting in crashes, hitting curbs, and taking out mailboxes.

“A little worried about your car?”

“Ja, her driving tends to be a bit..”

“Chaotic?”

Caleb lets out a soft laugh, “I was going to say reckless but chaotic works too.”

Jester can see the soft smile he’s currently trying to control from the corner of her eye. A comfortable silence falls on them as Jester isn’t sure how to continue. _Just talk to him silly, he’s right there._ Jester fidgets with her pen nervously.

“I am sorry I called you a stinky hobo.”

Caleb presses his lips together before he responds, “Actually if I recall I was a dirty hobo.”

Jester wants to shrivel up in die face palming as he responds. _Stupid! Stupid! You get a second shot at talking with this guy and you blow it again._ Caleb watches as Jester sinks her face deeper into her hands. He wasn’t going to lie she looked sort of adorable. Typically, in situations like this he was the flustered one, stumbling over his words.

Caleb bit his lips nervously, “Would you like some sugar cookies? This shop has adorable little jack o lanterns iced on them.”

Jester head perks up from the table, “Really?”

Caleb can see the adorable joy in her eyes which makes it impossible for him not to smile.

“How about you prepare our information on the fair while I go get us some tasty treats. Ja?”

Jester nods ecstatically, “That would be wonderful Cayleb.”

He gets up from his seat to head to the counter unaware that his cardigan is tangled in the chair. Suddenly he falls to the ground taking the wooden chare with him. Jester stares at him in shock unsure how to react. Caleb is mortified but as he stares at Jester’s shocked expression, he can’t help but chuckle. _Ja, should have known my smoothness could only last for so long._

“Seems you’re not the only one building an intimate relationship with the floor today, ja?”

Jester giggles at his comment offering him a hand up. He gladly takes it, admiring the way her blue curls bounce as she tilts her head.

“Are you okay Cayleb?”

“Ja, believe it or not, I am quite used to making a fool out of myself.”

Jester smiles at him shaking her head, “I was talking physically silly, you made quite a loud sound hitting the floor.” Jester takes his arm pulling up his sleeve and evaluates his arm. “Nothing’s broken but you’re going to have quite the bruise.”

Caleb looks at her intrigued, a look that alerts Jester to what she has done.

“Oh, I am sorry force of habit. I work as an EMT at our local hospital on nights and weekends.”

“Really?” He looked at her a bit confused like it wasn’t the answer he was expecting.

“Yea I got the two-year program done when I was unsure what I wanted to study still. Now it’s my very ‘exciting’ part-time job while I’m making my way to becoming a nurse.”

“You don’t sound all that enthusiastic about it.”

Jester looks up at him furrowing her brow, “Oh no don’t get me wrong I love helping people. I just had bigger dreams than this. Though being a struggling artist doesn’t exactly pay the rent, so I’ll consider myself lucky I have a natural talent in medicine.”

Jester’s cheeks are slightly tinted red as she rambled. Caleb can’t help but find her utterly endearing, as she rocks on her heels a bit. 

“Well if you don’t mind, I’m going to go get us our cookies. When I get back, we can talk about the spooky event we have planned.” Caleb bit his lip for a moment. “And maybe you could even show me some of your art.”

Jester smile grows as she nods, “Just be careful this time Cayleb, wouldn’t want you getting hurt over cookies.”

He chuckles in response, “It’s alright didn’t you hear I have an EMT with me.”

Caleb wanted to kick himself the moment the words left his lips. _Scheiße,_ _you idiot you sounded so lame!_ Though to his surprise, it just made Jester smile grow wider. Turning around he begins to make his way to the counter once more. Only faintly hearing Jester giggle softly.

“Don’t worry… I got you.”

**Notes for the Chapter:**

> Ps. Promise next chapter will start getting spooky :)

**Author's Note:**

> Thank you for reading :) Tell me what ya think


End file.
